The East Broad Top Railroad constructed a tunnel through Sideling Hill in 1873–74 as part of its mainline construction. The tunnel predates the South Pennsylvania Railroad tunnel construction 11 miles (18 km) to the south by eight years. The tunnel is single-tracked, and curved at each end. It originally had a stone portal on its eastern (RR North) end and a natural stone portal at its western (RR South) end, but about 1919 the north portal was replaced with a concrete one.

The north portal was equipped with doors to prevent wind from blowing through the tunnel as the wind caused water percolating into the tunnel to freeze on the tracks in the winter. In 1911, this ice caused the brand new locomotive #12 to derail its pilot axle inside the tunnel then derail the entire locomotive at the Kimmel switch just beyond the tunnel. In the 1940s, the doors were equipped with remote actuators mounted on poles a few hundred feet before each portal. This allowed the crews to open and close the doors without stopping. The system did not work flawlessly and a door was ripped off by a caboose cupola.

The tunnel was in service from 1874 until the railroad ceased operations in 1956. The line is technically out of service (but not abandoned), and the track is still in place through the tunnel, although not serviceable. The tunnel and rail line are private property and not open to the public.

The tunnel, the longest of the seven original turnpike tunnels at 6,782 feet (2,067 m) long, was used from the turnpike's opening in 1940 until 1968. Due to increasing traffic on the highway, the turnpike commission began upgrading all of its two-lane tunnels, constructing twin bores for its tunnels through the Allegheny, Tuscarora, Kittatinny, and Blue mountains, and bypassing the tunnels under Laurel Hill, Rays Hill, and Sideling Hill with new, six-lane highways climbing the adjacent hills. The Sideling Hill tunnel and the nearby Rays Hill tunnel, along with connecting segments of four-lane highway, were used for many years as a testing facility for new highway technologies.[citation needed]

A highway rest stop, located near the eastern side of the Sideling Hill Road Cut on Interstate 68 west of Hancock, includes a pedestrian bridge crossing I-68, connecting the eastbound and westbound rest areas and offering views of the cut, in which stopping is prohibited.

The rest stop formerly included the Sideling Hill Exhibit Center, a four-level geological museum and travel information center which opened in 1991. Due to state budget cuts, this facility was closed on Aug. 15, 2009, as part of a $280 million budget reduction package, saving the state about $110,000 annually. Before its closing, the center served about 95,000 visitors a year.[5] Many of the geological exhibits from the former Exhibit Center are now displayed at the Hancock Museum in nearby Hancock, Maryland.[4][6]

The former Exhibit Center building was reopened as a Welcome Center on October 9, 2015. Only part of the facility is open, with the former Exhibit Center exhibits remaining at the Hancock Museum.[7]